Lessons from Early Microsoft Days

Rich Barton is the co-founder and co-executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow, Rich founded Expedia within Microsoft in 1994 and successfully spun the company off as a public company in 1999. He served as president, CEO, and board director of Expedia and later co-founded and served as non-executive chairman of Glassdoor.

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Timestamps:

[00:00:00] Start.

[00:05:30] Eddy Cue magic.

[00:06:14] Rich’s morning routine and workout philosophy.

[00:13:38] How Brad Chase at Microsoft taught Rich to swing big.

[00:15:46] The failed DOS for Dummies book bundle project.

[00:18:52] Steering a company toward a culture of innovation.

[00:20:26] Rich’s journey from management consulting to Microsoft.

[00:24:34] How Expedia came to be.

[00:32:32] Pitching and recruiting team talent.

[00:37:18] Degree design at Stanford.

[00:39:45] Realizing the value of real work as a youth.

[00:41:44] A fascination with Italy.

[00:43:01] Selling Expedia to Barry Diller/IAC.

[00:43:51] Dara Khosrowshahi’s role in Expedia’s acquisition.

[00:45:23] From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink.

[00:55:41] “Big pond, good fishermen” as business criteria.

[00:56:50] Early Zillow mistakes.

[01:00:05] The Zestimate: Zillow’s killer feature.

[01:01:29] Making lemonade from the lemons of Zillow’s launch day server crash.

[01:03:49] Rich’s provocation marketing playbook.

[01:05:30] Regulatory battles and resistance to industry disruption.

[01:10:44] Founding Glassdoor and its “give to get” data collection model.

[01:12:58] Avvo and rating attorneys — legal challenges as marketing.

[01:16:11] Digital marketplaces and Google disintermediation concerns.

[01:19:52] How Rich names companies to be memorable.

[01:25:28] Why Rich recommends leaving fear out of the provocation marketing equation.

[01:26:48] Working with Benchmark Capital.

[01:30:37] What serving on a board looks like and Rich’s membership criteria: “Is it local? Is it fun? Is it lucrative?”

[01:39:00] Rich’s motivation and regimen for staying healthy in his 50s.

[01:47:13] Cultivating leadership through absence — the two-week disconnected trip.

[01:49:34] Building a good company by keeping good company.

[01:51:42] Developing the skill to fire people as a win/win proposition.

[01:54:41] Rich’s family tattoo design and symbolism.

[01:57:29] Advice for balancing family and professional life.

[02:01:08] The benefits of distributed workforces post-pandemic.

[02:03:23] Recommended reading.

[02:12:17] Rich’s billboard.

[02:14:25] The importance of sabbaticals and disconnecting from digital devices.

[02:17:41] Taking up Procreate digital art during COVID.

[02:19:05] Parting thoughts.

*

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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.

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